Compound and organic light-emitting device including the same

ABSTRACT

A compound, an organic light-emitting device, and a display device, the compound represented by Formula 1:

CROSS-REFERENCE TO RELATED APPLICATION

Korean Patent Application No. 10-2015-0049076, filed on Apr. 7, 2015, inthe Korean Intellectual Property Office, and entitled: “Compound andOrganic Light-Emitting Device Comprising the Same,” is incorporated byreference herein in its entirety.

BACKGROUND

1. Field

Embodiments relate to a compound and an organic light-emitting deviceincluding the compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emitting devices thathave advantages such as wide viewing angles, excellent contrast, quickresponse, high brightness, excellent driving voltage characteristics,and can provide multicolored images.

An organic light-emitting device may have a structure in which a firstelectrode, a hole transport region, an emission layer, an electrontransport region, and a second electrode are sequentially disposed inthis order on a substrate. Holes injected from the first electrode moveto the emission layer via the hole transport region, while electronsinjected from the second electrode move to the emission layer via theelectron transport region. Carriers such as the holes and electronsrecombine in the emission layer to generate excitons. When the excitonsdrop from an excited state to a ground state, light is emitted.

SUMMARY

Embodiments are directed to a compound and an organic light-emittingdevice including the compound.

The embodiments may be realized by providing a compound represented byFormula 1:

wherein, in Formula 1, R₁ to R₃ are each independently selected from asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, and a group represented by Formula 1-1; and atleast one of R₁ to R₃ is a group represented by Formula 1-1:

wherein, in Formula 1-1, X is selected from a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group; mis an integer of 1 to 3, a plurality of Xs being the same or differentwhen m is 2 or 3; and Ar₁ and Ar₂ are each independently selected from asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,wherein at least one substituent of the substituted C₁-C₆₀ alkyl group,the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynylgroup, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group, thesubstituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ arylene group, the substituted C₆-C₆₀ aryloxy group,the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀ heteroarylgroup, the substituted C₁-C₆₀ heteroarylene group, the substitutedmonovalent non-aromatic condensed polycyclic group, the substitutedmonovalent non-aromatic condensed heteropolycyclic group, thesubstituted divalent non-aromatic condensed polycyclic group, and thesubstituted divalent non-aromatic condensed heteropolycyclic group isselected from: a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, and a C₁-C₆₀ alkoxy group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₆₀ alkoxy group, each substitutedwith at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇), a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group,and a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇), wherein Q₁₁ to Q₁₇ and Q₂₁ to Q₂₇are each independently selected from a hydrogen, a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group; and

a plurality of Xs are the same or differs when m is 2 or greater.

In Formula 1-1, X may be a substituted or unsubstituted C₆-C₆₀ arylenegroup or a substituted or unsubstituted C₁-C₆₀ heteroarylene group.

In Formula 1-1, X is a group represented by one of Formulae 2a, 2b, and2c:

wherein, in Formulae 2a, 2b, and 2c, * indicates a binding site to anadjacent atom.

In Formula 1, Ar₁ and Ar₂ may each independently be a substituted orunsubstituted C₆-C₆₀ aryl group or a substituted or unsubstituted C₁-C₆₀heteroaryl group.

In Formula 1, Ar₁ and Ar₂ may each independently be a group representedby one of Formulae 3a, 3b, and 3c:

wherein, in Formulae 3a, 3b, and 3c, H₁ may be O or S; Z₁ may beselected from a hydrogen, a deuterium, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, asubstituted or unsubstituted C1-C20 heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group; p may be an integer of 1 to 7; and * indicates abinding site to a neighboring atom.

Z₁ may be a hydrogen, a deuterium, or a group represented by Formula 4a:

wherein, in Formula 4a, * indicates a binding site to a neighboringatom.

The compound represented by Formula 1 may be represented by Formula 2:

wherein, in Formula 2, X, m, Ar₁, and Ar₂ are defined the same as X, m,Ar₁, and Ar₂ of Formula 1.

The compound represented by Formula 1 may be represented by Formula 3:

wherein, in Formula 3, X, m, Ar₁, and Ar₂ are defined the same as X, m,Ar₁, and Ar₂ of Formula 1.

The compound represented by Formula 1 may be one of the followingCompounds 1 to 44, 46, and 47:

The embodiments may be realized by providing an organic light-emittingdevice including a first electrode; a second electrode disposed oppositeto the first electrode; and an organic layer between the first electrodeand the second electrode, the organic layer including an emission layer,wherein the organic layer includes the compound according to anembodiment.

The first electrode may be an anode, the second electrode may be acathode, and the organic layer may include a hole transport regionbetween the first electrode and the emission layer, the hole transportregion including at least one of a hole injection layer, a holetransport layer, and an electron blocking layer, and an electrontransport region between the emission layer and the second electrode,the electron transport region including at least one of a hole blockinglayer, an electron transport layer, and an electron injection layer.

The hole transport region may include the compound.

The hole transport region may include the hole transport layer; and thehole transport layer may include the compound.

The hole transport region may further include a charge-generatingmaterial.

The charge-generating material may include a p-dopant.

The p-dopant may include one of a quinone derivative, a metal oxide, anda cyano group-containing compound.

The electron transport region may include a metal complex.

The electron transport region may include a Li complex.

The electron transport region may include ET-D1 or ET-D2:

The embodiments may be realized by providing a display device includinga thin film transistor, the thin film transistor including a sourceelectrode and a drain electrode; and the organic light-emitting deviceaccording to an embodiment, wherein the first electrode of the organiclight-emitting device is electrically connected to the source electrodeor the drain electrode of the thin film transistor.

BRIEF DESCRIPTION OF THE DRAWING

Features will be apparent to those of skill in the art by describing indetail exemplary embodiments with reference to the attached drawing inwhich:

FIG. 1 illustrates a schematic view of a structure of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawings; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey exemplary implementations to those skilled in the art.

In the drawing figures, the dimensions of layers and regions may beexaggerated for clarity of illustration. It will also be understood thatwhen a layer or element is referred to as being “on” another layer orelement, it can be directly on the other layer or element, orintervening layers may also be present. Further, it will be understoodthat when a layer is referred to as being “under” another layer, it canbe directly under, and one or more intervening layers may also bepresent. In addition, it will also be understood that when a layer isreferred to as being “between” two layers, it can be the only layerbetween the two layers, or one or more intervening layers may also bepresent. Like reference numerals refer to like elements throughout.

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of,” when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.

According to an aspect of the present disclosure, there is provided acompound represented by Formula 1, below.

In Formula 1, R₁ to R₃ may each independently be selected from orinclude, e.g., a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, agroup represented by Formula 1-1, below, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In an implementation, at least one of R₁ to R₃ may be a grouprepresented by Formula 1-1.

In Formula 1-1,

X may be selected from or include, e.g., a substituted or unsubstitutedC₆-C₆₀ arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group.

m may be an integer of 1 to 3. In an implementation, a plurality of Xsmay be the same or different when m is 2 or 3.

Ar₁ and Ar₂ may each independently be selected from or include, e.g., asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,

In an implementation, at least one substituent of the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, and

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇).

Q₁₁ to Q₁₇ and Q₂₁ to Q₂₇ may each independently be selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

A fluorene derivative or an anthracene derivative may be used as a holetransport material. An organic light-emitting device with a holetransport layer including such a hole transport material may not havesatisfactory lifetime, efficiency, and power consumptioncharacteristics.

Benzochrysene may be used as a hole transport material. However, usingbenzochrysene in a hole transport layer may also provide unsatisfactorycharacteristics.

The embodiments may provide a compound that may have improved electricalstability, improved hole transport ability, and a glass transitiontemperature that is high enough to help prevent crystallization byinclusion of a compound and that may be suitable for a fluorescent orphosphorescent organic light-emitting device of any color, includingred, green, blue, and white. The embodiments may provide an organiclight-emitting device with high efficiency, low voltage, high luminance,and long lifespan by inclusion of the compound.

Hereinafter, substituents in Formula 1 will be described in greaterdetail.

In an implementation, in Formula 1-1, X may be or include, e.g., asubstituted or unsubstituted C₆-C₆₀ arylene group or a substituted orunsubstituted C₁-C₆₀ heteroarylene group.

In an implementation, in Formula 1-1, X may be a group represented byone of the following Formulae 2a, 2b, and 2c.

In Formulae 2a, 2b, and 2c, * indicates a binding site to a neighboringatom.

In an implementation, in Formula 1, Ar₁ and Ar₂ may each independentlybe or include, e.g., a substituted or unsubstituted C₆-C₆₀ aryl group ora substituted or unsubstituted C₁-C₆₀ heteroaryl group.

In an implementation, in Formula 1, An and Ar₂ may each independently bea group represented by one of the following Formulae 3a, 3b, and 3c.

In Formulae 3a, 3b, and 3c, H₁ may be, e.g., O or S.

Z₁ may be selected from or include, e.g., a hydrogen, a deuterium, asubstituted or unsubstituted C1-C20 alkyl group, a substituted orunsubstituted C6-C20 aryl group, a substituted or unsubstituted C1-C20heteroaryl group, a substituted or unsubstituted monovalent non-aromaticcondensed polycyclic group, and a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group.

p may be an integer of, e.g., 1 to 7.

* indicates a binding site to a neighboring atom.

In an implementation, in Formulae 3a, 3b, and 3c, Z₁ may be, e.g., oneof a hydrogen, a deuterium, and a group represented by the followingFormula 4a.

In Formula 4a, * indicates a binding site to a neighboring atom.

In an implementation, the compound represented by Formula 1 may berepresented by the following Formula 2.

In an implementation, the compound represented by Formula 1 may berepresented by the following Formula 3.

In Formulae 2 and 3, substituents (X, m, Ar₁, and Ar₂) may be definedthe same as those described herein with respect to Formula 1.

In an implementation, the compound represented by Formula 1 may be oneof the following Compounds 1 to 44, 46, and 47.

As used herein, the term “organic layer” refers to a single layer and/ora plurality of layers disposed between the first and second electrodesof the organic light-emitting device. Materials included in the “organiclayer” are not limited to organic materials.

Hereinafter, a structure of an organic light-emitting device accordingto an embodiment and a method of manufacturing the same will now bedescribed with reference to FIG. 1.

FIG. 1 illustrates a schematic cross-sectional view of an organiclight-emitting according to an embodiment. Referring to FIG. 1, theorganic light-emitting device 10 may include a first electrode 110, anorganic layer 150, and a second electrode 190.

A substrate may be disposed under the first electrode 110 or on thesecond electrode 190 in FIG. 1. The substrate may be a glass ortransparent plastic substrate with good mechanical strength, thermalstability, transparency, surface smoothness, ease of handling, and waterresistance.

For example, the first electrode 110 may be formed by depositing orsputtering a first electrode-forming material on the substrate 11. Whenthe first electrode 110 is an anode, a material having a high workfunction may be used as the first electrode-forming material tofacilitate hole injection. The first electrode 110 may be a reflectiveelectrode, a semi-transmissive electrode, or a transmissive electrode.Transparent and conductive materials such as ITO, IZO, SnO₂, and ZnO maybe used to form the first electrode. The first electrode 110 as asemi-transmissive electrode or a reflective electrode may be formed ofat least one material selected from magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag).

The first electrode 110 may have a single-layer structure or amulti-layer structure including a plurality of layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO.

The organic layer 150 may be disposed on the first electrode 110. Theorganic layer 150 may include an emission layer (EML).

The organic layer 150 may further include a hole transport regionbetween the first electrode and the EML, and/or an electron transportregion between the EML and the second electrode.

For example, the hole transport region may include at least one of ahole transport layer (HTL), a hole injection layer (HIL), a bufferlayer, and an electron blocking layer (EBL). For example, the electrontransport layer may include at least one of a hole blocking layer (HBL),an electron transport layer (ETL), and an electron injection layer(EIL).

The hole transport region may have a single-layered structure includinga single material, a single-layered structure including a plurality ofmaterials, or a multi-layered structure including a plurality of layersincluding different materials.

In an implementation, the electron transport region may have asingle-layered structure including a plurality of materials, or amulti-layered structure of HIL/HTL, HIL/HTL/buffer layer, HIL/bufferlayer, HTL/buffer layer, or HIL/HTL/EBL, wherein these layers forming amulti-layered structure are sequentially disposed on the first electrode110 in the order stated above.

When the hole transport region includes a HIL, the HIL may be formed onthe first electrode 110 by using any of a variety of methods, e.g., byusing vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, inkjet printing, laser printing, laser induced thermalimaging (LITI), or the like.

When the HIL is formed using vacuum deposition, the depositionconditions may vary depending on the material that is used to form theHIL and the structure of the HIL. For example, the deposition conditionsmay be selected from the following conditions: a deposition temperatureof about 100° C. to about 500° C., a degree of vacuum of about 10⁻⁸ toabout 10⁻³ torr, and/or a deposition rate of about 0.01 to 100 Å/sec.

When the HIL is formed using spin coating, the coating conditions mayvary depending on the material that is used to form the HIL and thestructure of the HIL. For example, the coating conditions may beselected from the following conditions: a coating rate of about 2,000rpm to about 5,000 rpm and a heat treatment temperature of about 80° C.to about 200° C.

When the hole transport region includes a HTL, the HTL may be formed onthe first electrode 110 or the HIL by using any of a variety of methods,e.g., by using vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing,laser induced thermal imaging (LITI), or the like. When the HTL isformed using vacuum deposition or spin coating, the conditions fordeposition and coating may be similar to the above-described depositionand coating conditions for forming the HIL, and accordingly will not bedescribed in detail.

In an implementation, the hole transport region may include at least oneof m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,α-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), and a compoundaccording to an embodiment.

For example, the HTL may include at least one of the compounds accordingto any of the embodiments.

The thickness of the hole transport region may be from about 100 Å toabout 10,000 Å, e.g., from about 100 Å to about 1,000 Å. When the holetransport region includes a HIL and a HTL, a thickness of the HIL may befrom about 100 Å to about 10,000 Å, e.g., from about 100 Å to about1,000 Å, and a thickness of the HTL may be from about 50 Å to about2,000 Å, e.g., from about 100 Å to about 1,500 Å. When the thicknessesof the hole transport region, the HIL, and the HTL are within theseranges, satisfactory hole transport characteristics may be obtainedwithout a substantial increase in driving voltage.

The hole transport region may further include a charge-generatingmaterial to help improve conductivity, in addition to the materials asdescribed above. The charge-generating material may be homogeneously orheterogeneously dispersed in the hole transport region.

The charge-generating material may be, e.g., a p-dopant. The p-dopantmay include one of quinone derivatives, metal oxides, and cyanogroup-containing compounds. Non-limiting examples of the p-dopant mayinclude quinone derivatives such as tetracyanoquinonedimethane (TCNQ),2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), andthe like; metal oxides such as tungsten oxide, molybdenum oxide, and thelike; and Compound HT-D1.

The hole transport region may further include a buffer layer, inaddition to the EBL, HIL, and HTL described above. The buffer layer maycompensate for an optical resonance distance of light according to awavelength of the light emitted from the EML, and thus may help improvelight-emission efficiency. A material in the buffer layer may includeany suitable material used in the hole transport region. The EBL mayblock migration of electrons from the electron transport region intoEML.

The EML may be formed on the first electrode 110 or the hole transportregion by using any of a variety of methods, e.g., by using vacuumdeposition, spin coating, casting, Langmuir-Blodgett (LB) deposition,inkjet printing, laser printing, laser induced thermal imaging (LITI),or the like. When the EML is formed using vacuum deposition or spincoating, the deposition and coating conditions for forming the EML maybe similar to the above-described deposition and coating conditions forforming the HIL, and accordingly will not be described in detail

When the organic light-emitting device 10 is a full color organiclight-emitting device, the EML may be patterned into a red emissionlayer, a green emission layer, and a blue emission layer to correspondto individual subpixels, respectively. In an implementation, the EML mayhave a structure in which a red emission layer, a green emission layerand a blue emission layer are stacked upon one another, or a structureincluding a mixture of a red light-emitting material, a greenlight-emitting material, and a blue light-emitting material withoutseparation of layers for the different color emission, and thus may emitwhite light.

The EML may include a host and a dopant.

The host may include, e.g., at least one of TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, and TCP.

In an implementation, the host may include a compound represented byFormula 301.

Ar₃₀₁-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb2)  <Formula 301>

In Formula 301,

Ar₃₀₁ may be selected from

a naphthalene group, a heptalene group, a fluorene group, aspiro-fluorene group, a benzofluorene group, a dibenzofluorene group, aphenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, and an indenoanthracene group, and

a naphthalene group, a heptalene group, a fluorene group, aspiro-fluorene group, a benzofluorene group, a dibenzofluorene group, aphenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, and an indenoanthracene group, each substituted withat least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (where Q₃₀₁to Q₃₀₃ are each independently selected from a hydrogen, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₆-C₆₀ aryl group, and a C₁-C₆₀heteroaryl group);

L₃₀₁ may be selected from

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorene group, a dibenzofluorenegroup, a phenanthrenylene group, an anthracenylene group, a pyrenylenegroup, a chrysenylene group, a pyridinylene group, a pyrazinylene group,a pyrimidinylene group, a pyridazinylene group, a quinolinylene group,an isoquinolinylene group, a quinoxalinylene group, a quinazolinylenegroup, a carbazolylene group, and a triazinylene group, and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one of a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

R₃₀₁ may be selected from

a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group, each substituted withat least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxyl group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

xb1 may be selected from 0, 1, 2, and 3; and

xb2 may be selected from 1, 2, 3, and 4.

For example, in Formula 301,

L₃₀₁ may be selected from

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group, and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group, each substitutedwith at least one selected from a deuterium, —F, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, and a chrysenyl group; and

R₃₀₁ may be selected from

a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group, each substituted withat least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group,each substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxyl groupor a salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and achrysenyl group.

In some other embodiments, the host may include a compound representedby Formula 301A.

In Formula 301A, substituents may be defined the same as those describedherein.

The compound of Formula 301 may include at least one of Compounds H1 toH42.

In an implementation, the host may include at least one of Compounds H43to H49.

The dopant for the EML may include at least one of a fluorescent dopantand a phosphorescent dopant.

The phosphorescent dopant may include an organic metal complexrepresented by Formula 401.

In Formula 401,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), halfnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm),

X₄₀₁ to X₄₀₄ may be each independently a nitrogen or a carbon,

A₄₀₁ and A₄₀₂ ring may be each independently selected from a substitutedor unsubstituted benzene group, a substituted or unsubstitutednaphthalene group, a substituted or unsubstituted fluorene group, asubstituted or unsubstituted spiro-fluorene group, a substituted orunsubstituted indene group, a substituted or unsubstituted pyrrolegroup, a substituted or unsubstituted thiophene group, a substituted orunsubstituted furan group, a substituted or unsubstituted imidazolegroup, a substituted or unsubstituted pyrazole group, a substituted orunsubstituted thiazole group, a substituted or unsubstituted isothiazolegroup, a substituted or unsubstituted oxazole group, a substituted orunsubstituted isooxazole group, a substituted or unsubstituted pyridinegroup, a substituted or unsubstituted pyrazine group, a substituted orunsubstituted pyrimidine group, a substituted or unsubstitutedpyridazine group, a substituted or unsubstituted quinoline group, asubstituted or unsubstituted isoquinoline group, a substituted orunsubstituted benzoquinoline group, a substituted or unsubstitutedquinoxaline group, a substituted or unsubstituted quinazoline group, asubstituted or unsubstituted carbazole group, a substituted orunsubstituted benzoimidazole group, a substituted or unsubstitutedbenzofuran group, a substituted or unsubstituted benzothiophene group, asubstituted or unsubstituted isobenzothiophene group, a substituted orunsubstituted benzoxazole group, a substituted or unsubstitutedisobenzoxazole group, a substituted or unsubstituted triazole group, asubstituted or unsubstituted oxadiazole group, a substituted orunsubstituted triazine group, a substituted or unsubstituteddibenzofuran group, and a substituted or unsubstituted dibenzothiophenegroup,

at least one substituent of the substituted benzene group, thesubstituted naphthalene group, the substituted fluorene group, thesubstituted spiro-fluorene group, the substituted indene group, thesubstituted pyrrole group, the substituted thiophene group, thesubstituted furan group, the substituted imidazole group, thesubstituted pyrazole group, the substituted thiazole group, thesubstituted isothiazole group, the substituted oxazole group, thesubstituted isooxazole group, the substituted pyridine group, thesubstituted pyrazine group, the substituted pyrimidine group, thesubstituted pyridazine group, the substituted quinoline group, thesubstituted isoquinoline group, the substituted benzoquinoline group,the substituted quinoxaline group, the substituted quinazoline group,the substituted carbazole group, the substituted benzoimidazole group,the substituted benzofuran group, the substituted benzothiophene group,the substituted isobenzothiophene group, the substituted benzoxazolegroup, the substituted isobenzoxazole group, the substituted triazolegroup, the substituted oxadiazole group, the substituted triazine group,the substituted dibenzofuran group, and the substituted dibenzothiophenegroup may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid group or asalt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid group or asalt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₄₀₁)(Q₄₀₂),—Si(Q₄₀₃)(Q₄₀₄)(Q₄₀₅), and —B(Q₄₀₆)(Q₄₀₇),

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group,

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₄₁₁)(Q₄₁₂), —Si(Q₄₁₃)(Q₄₁₄)(Q₄₁₅),and —B(Q₄₁₆)(Q₄₁₇), and

—N(Q₄₂₁)(Q₄₂₂), —Si(Q₄₂₃)(Q₄₂₄)(Q₄₂₅), and —B(Q₄₂₆)(Q₄₂₇);

L₄₀₁ may be an organic ligand;

xc1 may be 1, 2, or 3; and

xc2 may be 0, 1, 2, or 3.

For example, L₄₀₁ may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₁ may be selected from a halogen ligand (forexample, Cl or F), a diketone ligand (for example, acetylacetonate,1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate,or hexafluoroacetonate), a carboxylic acid ligand (for example,picolinate, dimethyl-3-pyrazole carboxylate, or benzoate), a carbonmonoxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorousligand (for example, phosphine or phosphite).

When A₄₀₁ in Formula 401 has at least two substituents, the at least twosubstituents of A₄₀₁ may be linked to each other to form a saturated orunsaturated ring.

When A₄₀₂ in Formula 401 has at least two substituents, the at least twosubstituents of A₄₀₂ may be linked to each other to form a saturated orunsaturated ring.

When xc1 in Formula 401 is 2 or greater, the plurality of ligands inFormula 401, represented by

may be identical or differ. When xc1 in Formula 401 is 2 or greater,A₄₀₁ and A₄₀₂ may be linked to A₄₀₁ and A₄₀₂ of another adjacent liganddirectly or via a linker (for example, a C₁-C₅ alkylene group, —N(R′)—(where R′ is a C₁-C₁₀ alkyl group or a C₆-C₂₀ aryl group), or —C(═O)—).

The fluorescent dopant may include at least one of Compounds PD1 toPD74.

For example, the phosphorescent dopant may include PtOEP.

For example, the fluorescent dopant may include at least one of DPAVBi,BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

For example, the fluorescent dopant may include a compound representedby Formula 501.

In Formula 501,

Ar₅₀₁ may be selected from

a naphthalene group, a heptalene group, a fluorene group, aspiro-fluorene group, a benzofluorene group, a dibenzofluorene group, aphenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, and an indenoanthracene group, and

a naphthalene group, a heptalene group, a fluorene group, aspiro-fluorene group, a benzofluorene group, a dibenzofluorene group, aphenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, and an indenoanthracene group, each substituted withat least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₂—C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ hetero aryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (where Q₅₀₁to Q₅₀₃ are each independently selected from a hydrogen, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₆-C₆₀ aryl group, and a C₁-C₆₀heteroaryl group),

L₅₀₁ to L₅₀₃ may be defined the same as described above herein inconjunction with L₃₀₁;

R₅₀₁ and R₅₀₂ may be each independently selected from

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazole group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, and adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

xd1 to xd3 are each independently selected from 0, 1, 2, and 3; and

xb4 is selected from 1, 2, 3, and 4.

For example, the fluorescent dopant may include at least one ofCompounds FD1 to FD8.

The amount of the dopant in the EML may be from about 0.01 parts toabout 15 parts by weight based on 100 parts by weight of the host.

The thickness of the EML may be about 100 Å to about 1,000 Å, e.g.,about 200 Å to about 600 Å. When the thickness of the EML is withinthese ranges, the EML may have good light emitting ability without asubstantial increase in driving voltage.

Next, the electron transport region may be formed on the EML.

The electron transport region may include at least one of a HBL, an ETL,and an EIL.

When the electron transport region includes a HBL, the HBL may be formedon the EML by using any of a variety of methods, e.g., by using vacuumdeposition, spin coating, casting, Langmuir-Blodgett (LB) deposition,inkjet printing, laser printing, laser induced thermal imaging (LITI),or the like. When the HBL is formed using vacuum deposition or spincoating, the deposition and coating conditions for forming the HBL maybe similar to the above-described deposition and coating conditions forforming the HIL, and accordingly will not be described in detail.

For example, the HBL may include at least one of BCP and Bphen.

The thickness of the HBL may be from about 20 Å to about 1,000 Å, e.g.,about 30 Å to about 300 Å. When the thickness of the HBL is within theseranges, the HBL may have satisfactory hole blocking characteristicswithout a substantial increase in driving voltage.

The electron transport region may have a stack structure including ETLand EIL, or HBL, ETL, and EIL that are sequentially stacked on the EMLin the stated order.

In an implementation, the organic layer 150 of the organiclight-emitting device may include an electron transport region disposedbetween the EML and the second electrode 190 and including an ETL. TheETL may include multiple layers. For example, the ETL may include afirst electron transport layer and a second electron transport layer.

The ETL may include at least one of BCP, Bphen, Alq₃, Balq, TAZ, andNTAZ.

In an implementation, the ETL may include at least one of compoundsrepresented by Formulae 601 and 602.

Ar₆₀₁-[(L₆₀₁)_(xe1)-E₆₀₁]_(xe2)  <Formula 601>

In Formula 601,

Ar₆₀₁ may be selected from

a naphthalene group, a heptalene group, a fluorene group, aspiro-fluorene group, a benzofluorene group, a dibenzofluorene group, aphenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, and an indenoanthracene group, and

a naphthalene group, a heptalene group, a fluorene group, aspiro-fluorene group, a benzofluorene group, a dibenzofluorene group, aphenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, and an indenoanthracene group, each substituted withat least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ hetero aryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (where Q₃₀₁to Q₃₀₃ are each independently selected from a hydrogen, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₆-C₆₀ aryl group, and a C₁-C₆₀heteroaryl group);

L₆₀₁ may be defined the same as described above herein in conjunctionwith L₃₀₁;

E₆₀₁ may be selected from

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, and

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coroneryl group, anobarenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzooxazolylgroup, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group;

xe1 may be selected from 0, 1, 2, and 3; and

xe2 may be selected from 1, 2, 3, and 4.

In Formula 602,

X₆₁₁ may be N or C-(L₆₁₁)_(xe611)-R₆₁₁, X₆₁₂ may be N orC-(L₆₁₂)_(xe612)-R₆₁₂, X₆₁₃ may be N or C-(L₆₁₃)_(xe613)-R₆₁₃, at leastone of X₆₁₁ to X₆₁₃ may be N;

L₆₁₁ to L₆₁₆ may be defined the same as described above in conjunctionL₃₀₁;

R₆₁₁ to R₆₁₆ may be each independently selected from

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

xe611 to xe616 may be each independently selected from, 0, 1, 2, and 3.

The compound of Formula 601 and the compound of Formula 602 may eachindependently be selected from Compounds ET1 to ET15.

The thickness of the ETL may be from about 100 Å to about 1,000 Å, e.g.,from about 150 Å to about 500 Å. When the thickness of the ETL is withinthese ranges, the ETL may have satisfactory electron transportingability without a substantial increase in driving voltage.

In an implementation, the ETL may further include a metal-containingmaterial, in addition to the above-described materials.

The metal-containing material may include a lithium (Li) complex.Non-limiting examples of the Li complex may include compound ET-D1(lithium quinolate (LiQ)), and compound ET-D2.

The electron transport region may include an EIL that may facilitateinjection of electrons from the second electrode 190.

The EIL may be formed on the ETL by using any of a variety of methods,e.g., by using vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing,laser induced thermal imaging (LITI), or the like. When the EIL isformed using vacuum deposition or spin coating, the deposition andcoating conditions for forming the EIL may be similar to theabove-described deposition and coating conditions for forming the HIL,and accordingly will not be described in detail.

The EIL may include at least one selected from LiF, NaCl, CsF, Li₂O,BaO, and LiQ.

The thickness of the EIL may be from about 1 Å to about 100 Å, e.g.,from about 3 Å to about 90 Å. When the thickness of the EIL is withinthese ranges, the EIL may have satisfactory electron injection abilitywithout a substantial increase in driving voltage.

The second electrode 190 may be disposed on the organic layer 150, asdescribed above. The second electrode 190 may be a cathode as anelectron injecting electrode. A material for forming the secondelectrode 190 may be a metal, an alloy, an electrically conductivecompound, which have a low-work function, or a mixture thereof.Non-limiting examples of materials for forming the second electrode 190may include lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag). In an implementation, a material for formingthe second electrode 190 may include ITO or IZO. The second electrode190 may be a reflective electrode, a semi-transmissive electrode, or atransmissive electrode.

In an implementation, the organic layer 150 of the organiclight-emitting device 10 may be formed using a compound of Formula 1according to any of the above-described embodiments by deposition or awet process of coating a solution of a compound of Formula 1 accordingto any of the above-described embodiments.

In an implementation, the organic light-emitting device may be includedin various types of flat panel display devices, such as in a passivematrix organic light-emitting display device or in an active matrixorganic light-emitting display device. For example, when the organiclight-emitting device is included in an active matrix organiclight-emitting display device including a thin-film transistor, thefirst electrode on the substrate as a pixel electrode may beelectrically connected to a source electrode or a drain electrode of thethin-film transistor. In an implementation, the organic light-emittingdevice may also be included in a flat panel display devices having adouble-sided screen.

Hereinafter, substituents described with reference to the formulae willnow be described in detail. In this regard, the numbers of carbons insubstituents are presented only for illustrative purposes and do notlimit the characteristics of the substituents. The substituents notdefined herein are construed as having common meanings understood by oneof ordinary skill in the art.

As used herein, a C₁-C₆₀ alkyl group refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ alkyl group, a methyl group, anethyl group, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.A C₁-C₆₀ alkylene group refers to a divalent group having the samestructure as the C₁-C₆₀ alkyl.

As used herein, a C₁-C₆₀ alkoxy group refers to a monovalent grouprepresented by —OA₁₀₁ (where A₁₀₁ is a C₁-C₆₀) alkyl group, as describedabove. Non-limiting examples of the C₁-C₆₀ alkoxy group are a methoxygroup, an ethoxy group, and an isopropyloxy group.

As used herein, a C₂-C₆₀ alkenyl group refers to a hydrocarbon groupincluding at least one carbon double bond in the middle or terminal ofthe C₂-C₆₀ alkyl group. Non-limiting examples of the C₂-C₆₀ alkenylgroup are an ethenyl group, a prophenyl group, and a butenyl group. AC₂-C₆₀ alkylene group refers to a divalent group having the samestructure as the C₂-C₆₀ alkenyl group.

As used herein, a C₂-C₆₀ alkynyl group refers to a hydrocarbon groupincluding at least one carbon triple bond in the middle or terminal ofthe C₂-C₆₀ alkyl group. Non-limiting examples of the C₂-C₆₀ alkynylgroup are an ethynyl group, and a propynyl group. A C₂-C₆₀ alkynylenegroup used herein refers to a divalent group having the same structureas the C₂-C₆₀ alkynyl group.

As used herein, a C₃-C₁₀ cycloalkyl group refers to a monovalent,monocyclic hydrocarbon group having 3 to 10 carbon atoms. Non-limitingexamples of the C₃-C₁₀ cycloalkyl group are a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, and acycloheptyl group. A C₃-C₁₀ cycloalkylene group refers to a divalentgroup having the same structure as the C₃-C₁₀ cycloalkyl group.

As used herein, a C₁-C₁₀ heterocycloalkyl group refers to a monovalentmonocyclic group having 1 to 10 carbon atoms in which at least onehetero atom selected from N, O, P, and S is included as a ring-formingatom. Non-limiting examples of the C₂-C₁₀ heterocycloalkyl group are atetrahydrofuranyl group, and a tetrahydrothiophenyl group. A C₂-C₁₀heterocycloalkylene group refers to a divalent group having the samestructure as the C₂-C₁₀ heterocycloalkyl group.

As used herein, a C₃-C₁₀ cycloalkenyl group refers to a monovalentmonocyclic group having 3 to 10 carbon atoms that includes at least onedouble bond in the ring but does not have aromaticity. Non-limitingexamples of the C₃-C₁₀ cycloalkenyl group are a cyclopentenyl group, acyclohexenyl group, and a cycloheptenyl group. A C₃-C₁₀ cycloalkenylenegroup refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

As used herein, a C₂-C₁₀ heterocycloalkenyl group used herein refers toa monovalent monocyclic group having 2 to 10 carbon atoms that includesat least one double bond in the ring and in which at least one heteroatom selected from N, O, P, and S is included as a ring-forming atom.Non-limiting examples of the C₂-C₁₀ heterocycloalkenyl group are a2,3-hydrofuranyl group, and a 2,3-hydrothiophenyl group. A C₂-C₁₀heterocycloalkenylene group used herein refers to a divalent grouphaving the same structure as the C₂-C₁₀ heterocycloalkenyl group.

As used herein, a C₆-C₆₀ aryl group refers to a monovalent, aromaticcarbocyclic aromatic group having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group refers to a divalent, aromatic carbocyclic group having 6to 60 carbon atoms. Non-limiting examples of the C₆-C₆₀ aryl group are aphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenylgroup, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀ arylgroup, and the C₆-C₆₀arylene group include at least two rings, the ringsmay be fused to each other.

As used herein, a C₁-C₆₀ heteroaryl group refers to a monovalent,aromatic carbocyclic aromatic group having 1 to 60 carbon atoms and atleast one hetero atom selected from N, O, P, and S as a ring-formingatom. A C₁-C₆₀ heteroarylene group refers to a divalent, aromaticcarbocyclic group having 1 to 60 carbon atoms, and at least one heteroatom selected from N, O, P, and S as a ring-forming atom. Non-limitingexamples of the C₁-C₆₀ heteroaryl group are a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀ heteroarylene group include at least tworings, the rings may be fused to each other.

As used herein, a C₆-C₆₀ aryloxy group indicates —OA₁₀₂ (where A₁₀₂ is aC₆-C₆₀ aryl group, as described above), and a C₆-C₆₀ arylthio groupindicates —SA₁₀₃ (where A₁₀₃ is a C₆-C₆₀ aryl group, as describedabove).

As used herein, a monovalent non-aromatic condensed polycyclic group(including, for example, 8 to 60 carbon atoms) refers to a monovalentgroup that includes at least two rings condensed to each other andincludes only carbon atoms as ring-forming atoms and that representsnon-aromaticity as a whole. An example of the monovalent non-aromaticcondensed polycyclic group is a fluorenyl group. As used herein, adivalent non-aromatic condensed polycyclic group refers to a divalentgroup with the same structure as the monovalent non-aromatic condensedpolycyclic group.

As used herein, a monovalent non-aromatic condensed heteropolycyclicgroup (including, for example, 2 to 60 carbon atoms) refers to amonovalent group that includes at least two rings condensed to eachother and include carbon and hetero atoms selected from N, O, P and S asring-forming atoms and that represents non-aromaticity as a whole. Anexample of the monovalent non-aromatic condensed heteropolycyclic groupis a carbazolyl group. As used herein, a divalent non-aromatic condensedheteropolycyclic group refers to a divalent group with the samestructure as the monovalent non-aromatic condensed polycyclic group.

As used herein, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, the substituted C₂-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₂-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇),

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group,

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇), and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇),

wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇ and Q₃₁ to Q₃₇ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

For example, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, the substituted C₂-C₁₀ heterocycloalkylene group,substituted C₃-C₁₀ cycloalkenylene group, the substituted C₂-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group,

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅) and—B(Q₂₆)(Q₂₇), and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇),

wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group.

As used herein, “Ph” denotes a phenyl group, “Me” denotes a methylgroup, “Et” denotes an ethyl group, “ter-Bu” or “Bu^(t)” denotes atert-butyl group.

One or more embodiments of the present disclosure will now be describedin detail with reference to the following examples including synthesisexamples. However, these examples are only for illustrative purposes andare not intended to limit the scope of the one or more embodiments ofthe present disclosure.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

EXAMPLES Synthesis Example 1 Synthesis of Compound 1

(1) Synthesis of Intermediate 1-1

20.0 g (20 mmol) of 2-bromonaphthalene was dissolved in 50 mL oftetrahydrofuran (THF), and then 8.8 mL (22.0 mmol) of n-BuLi (2.5 M inhexane) was slowly dropwise added thereto at about −78° C. After thereaction solution was stirred at the same temperature for about 1 hour,4.65 mL (25.0 mmol) of2-isoproxy-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane was slowly dropwiseadded to the reaction solution, stirred at about −78° C. for about 1hour, and then further stirred at ambient temperature for about 24hours. After termination of the reaction, 30 mL of a 10% HCl aqueoussolution and 30 mL of H₂O were added thereto, followed by extractionthree times with 50 ml of diethyl ether. An organic phase was collectedand dried using magnesium sulfate, followed by evaporating the solvent.The resulting residue was purified by silica gel column chromatographyto obtain 3.7 g of Intermediate 1-1 (Yield: 73%). This compound wasidentified by liquid chromatography-mass spectrometry (LC-MS).C₁₆H₁₉BO₂: M⁺ 255.1

(2) Synthesis of Intermediate 1-2

2.5 g (10.0 mmol) of Intermediate 1-1, 3.4 g (11.0 mmol) of2-bromo-1-iodo-4-methoxy benzene, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, and2.1 g (15.0 mmol) of K₂CO₃ were dissolved in 40 mL of a mixed solutionof THF and H₂O (2:1 by volume) and stirred at about 80° C. for about 5hours. After the resulting reaction solution was cooled down to ambienttemperature, 40 mL of water was added thereto, followed by extractionthree times with 50 mL of diethyl ether. An organic phase was collectedand dried using magnesium sulfate, followed by evaporating the solvent.The resulting residue was purified by silica gel column chromatographyto obtain 2.3 g of Intermediate 1-2 (Yield: 72%). This compound wasidentified by LC-MS. C₁₇H₁₃BrO M⁺ 313.1

(3) Synthesis of Intermediate 1-3

3.13 g (10.0 mmol) of Intermediate 1-2, 2 g (10.0 mmol) of(2-bromophenyl)boronic acid, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, and 2.1 g(15.0 mmol) of K₂CO₃ were dissolved in 40 mL of a mixed solution of THFand H₂O (2:1 by volume) and stirred at about 80° C. for about 5 hours.After the resulting reaction solution was cooled down to ambienttemperature, 40 mL of water was added thereto, followed by extractionthree times with 50 mL of diethyl ether. An organic phase was collectedand dried using magnesium sulfate, followed by evaporating the solvent.The resulting residue was purified by silica gel column chromatographyto obtain 2.9 g of Intermediate 1-3 (Yield: 75%). This compound wasidentified by LC-MS. C₂₃H₁₇BrO M⁺ 389.1

(4) Synthesis of Intermediate 1-4

10 mmol of Intermediate 1-3, 1.4 mmol of palladium(II) acetate, 2.8 mmolof PCy₃-HBF₄, and 6 mmol of K₂CO₃ were dissolved in 100 mL ofN—N-dimethyl acetamide (DMA) and stirred at about 140° C. for about 4hours. After the resulting reaction solution was cooled down to ambienttemperature, 30 mL of water and 30 mL of toluene were added thereto,followed by extraction three times with 50 mL of diethyl ether. Anorganic phase was collected and dried using magnesium sulfate, followedby evaporating the solvent. The resulting residue was purified by silicagel column chromatography to obtain 2.2 g of Intermediate 1-4 (Yield:73%). This compound was identified by LC-MS. C₂₃H₁₆O M⁺ 309.1

(5) Synthesis of Intermediate 1-5

After 3.08 g (10 mmol) of Intermediate 1-4 was diluted with 500 mL ofdichloromethane, 15 mL of tribromoboron was slowly dropwise addedthereto. After about 3 hours, the reaction was terminated at about 0° C.with a saturated sodium bicarbonate aqueous solution, followed by phaseseparation to obtain an organic phase. The organic phase was dried usinganhydrous magnesium sulfate and concentrated under reduced pressure. Theresulting residue was purified by silica gel column chromatography toobtain 2.6 g of Intermediate 1-5 (Yield: 89%). This compound wasidentified by LC-MS. C₂₂H₁₄O M⁺ 295.1

(6) Synthesis of Intermediate 1-6

After 4.4 g (15 mmol) of Intermediate 1-5 was diluted with 600 mL ofdichloromethane, 31 mL of triethylamine was dropwise added thereto andthen 48 g of anhydrous trifluoroacetic acid was slowly dropwise addedthereto at about 0° C. The reaction solution was stirred at ambienttemperature for about 3 hours, and then the reaction was terminated withwater. An organic phase was collected, dried using anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The resultingresidue was purified by silica gel column chromatography to obtain 6.1 gof Intermediate 1-6 (Yield: 96%). This compound was identified by LC-MS.C₂₃H₁₃F₃O₃S M⁺ 427.1

(7) Synthesis of Intermediate 1-7

3.6 g of Intermediate 1-7 (Yield: 82%) was obtained in the same manneras in the synthesis of Intermediate 1-3, except that 4.3 g (10 mmol) ofIntermediate 1-6, instead of Intermediate 1-2, and 2.4 g of4-bromophenyl)boronic acid were used. This compound was identified byLC-MS. C₂₈H₁₇Br M⁺ 434.1

(8) Synthesis of Compound 1

4.3 g (10 mmol) of Intermediate 1-7, 3.7 g (22 mmol) of diphenylamine,0.36 g (0.4 mmol) of Pd₂(dba)₃, 0.04 g (0.4 mmol) of PtBu₃, and 4 g (40mmol) of KOtBu were dissolved in 80 mL of toluene and stirred at about85° C. for about 2 hours. The resulting reaction solution was cooleddown to ambient temperature, followed by extraction three times with 50mL of water and 50 mL of diethyl ether 50 mL. An organic phase wascollected and dried using magnesium sulfate, followed by evaporating thesolvent. The resulting residue was purified by silica gel columnchromatography to obtain 4.2 g of Compound 1 (Yield: 81%). This compoundwas identified by fast atom bombardment mass spectrometry (MS/FAB) and¹H nuclear magnetic resonance (NMR). C₄₀H₂₇N cal. 521.21. found 522.21.

¹H NMR (CDCl₃, 400 MHz) 9.01-8.99 (d, 2H), 8.71-8.64 (m, 2H), 8.46 (d,1H), 8.28-8.26 (d, 2H), 8.01-7.95 (m, 2H), 7.67-7.45 (m, 6H), 7.08-7.04(m, 4H), 6.85-6.84 (m, 2H), 6.66-6.63 (m, 2H), 6.16-6.13 (m, 4H)

Synthesis Example 2 Synthesis of Compound 23

(1) Synthesis of Intermediate 2-1

2.8 g (Yield: 91%) of Intermediate 2-1 was obtained in the same manneras in the synthesis of Intermediate 1-6, except that 2.7 g (15 mmol) of6-chloronaphthalene-2-ol, instead of Intermediate 1-5, was used. Thiscompound was identified by LC-MS. C₁₁H₆ClF₃O₃S M⁺ 311.1

(2) Synthesis of Intermediate 2-2

2.5 g (Yield: 77%) of Intermediate 2-2 was obtained in the same manneras in the synthesis of Intermediate 1-6, except that 3.1 g (10.0 mmol)of Intermediate 2-1, instead of Intermediate 1-2, was used. Thiscompound was identified by LC-MS. C₁₆H₁₀BrCl M⁺ 317.1

(3) Synthesis of Intermediate 2-3

3.1 g (Yield: 80%) of Intermediate 2-3 was obtained in the same manneras in the synthesis of Intermediate 1-6, except that 3.1 g (10.0 mmol)of Intermediate 2-2, instead of Intermediate 1-2, was used. Thiscompound was identified by LC-MS. C₂₂H₁₄BrCl M⁺ 317.1

(4) Synthesis of Intermediate 2-4

2.3 g (Yield: 75%) of Intermediate 2-4 was obtained in the same manneras in the synthesis of Intermediate 1-4, except that Intermediate 2-3,instead of Intermediate 1-3, was used. This compound was identified byLC-MS. C₂₂H₁₃C1 M⁺ 313.1

(5) Synthesis of Intermediate 2-5

3.6 g (Yield: 82%) of Intermediate 2-5 was obtained in the same manneras in the synthesis of Intermediate 1-7, except that 3.12 g (10 mmol) ofIntermediate 2-4, instead of Intermediate 1-6, was used. This compoundwas identified by LC-MS. C₂₈H₁₇Br M⁺ 433.1

(6) Synthesis of Compound 23

4.4 g (Yield: 85%) of Compound 23 was obtained in the same manner as inthe synthesis of Compound 1, except that 4.33 g (10 mmol) ofIntermediate 2-5, instead of Intermediate 1-7, was used. This compoundwas identified by MS/FAB and ¹H NMR. C₄₀H₂₇N cal. 521.21. found 522.21.

¹H NMR (CDCl₃, 400 MHz) 9.29 (s, 1H), 9.02 (s, 1H), 8.74-8.68 (m, 2H),8.52-8.48 (m, 2H), 8.39 (s, 1H), 8.07-8.05 (d, 1H), 7.90-7.88 (d, 1H),7.56-7.47 (m, 6H), 7.08-7.04 (m, 4H), 6.85-6.81 (m, 2H), 6.66-6.63 (m,2H), 6.16-6.13 (m, 4H)

Additional compounds were also synthesized using appropriateintermediate materials (for example, a corresponding compound withBr-substituent group, a corresponding boron compound, and the like) inthe same manner as in the above-described synthetic pathways (ofIntermediate 1-7 and Intermediate 2-5), and then identified by ¹H NMRand MS/FAB. The results are shown in Table 1.

Synthesis methods of other compounds not shown in Table 1 will also beobvious to those skilled in the art based on the above-describedsynthetic pathways and source materials.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 400 MHz) found calc. 1 δ =9.01-8.99 (d, 2H), 8.71-8.64 (m, 2H), 8.46 (d, 1H), 8.28-8.26 (d, 2H),522.21 521.21 8.01-7.95 (m, 2H), 7.67-7.45 (m, 6H), 7.08-7.04 (m, 4H),6.85-6.84 (m, 2H), 6.66-6.63 (m, 2H), 6.16-6.13 (m, 4H) 2 δ = 9.01-8.99(m, 2H), 8.71-8.66 (m, 2H), 8.46 (s, 1H), 8.28-8.26 (d, 1H), 572.23571.23 8.01-7.95 (m, 3H), 7.88 (m, 1H), 7.67-7.43 (m, 10H), 7.33 (d,1H), 7.14-7.04 (m, 3H), 6.66-6.57 (m, 3H), 6.24-6.22 (m, 2H) 5 δ =9.01-8.99 (m, 2H), 8.71-8.64 (m, 2H), 8.46 (s, 1H), 8.28-8.26 (d, 1H),674.28 673.28 8.01-7.95 (m, 3H), 7.67-7.35 (m, 15H), 6.85-6.81 (m, 4H),6.65-6.61 (m, 2H) 18 δ = 9.01-8.99 (d, 2H), 8.71-8.64 (m, 2H), 8.52 (s,1H), 8.30-8.27 (d, 1H), 724.29 723.29 8.18 (s, 1H), 8.03-7.96 (m, 3H),7.84-7.78 (m, 2H), 7.65-7.32 (m, 16H), 7.21-7.19 (m, 2H), 7.08-7.04 (m,3H), 6.93-6.92 (d, 2H), 6.16-6.14 (dd, 2H) 22 δ = 9.01-9.00 (m, 3H),8.75-8.69 (m, 2H), 8.50-8.48 (d, 1H), 8.36-8.34 (d, 523.21 522.21 1H),8.13 (d, 1H), 8.01-7.96 (m, 2H), 7.78-7.76 (ss, 1H), 7.67-7.45 (m, 4H),7.12-7.08 (m, 4H), 6.97-6.95 (d, 1H), 6.66-6.63 (m, 2H), 6.33-6.31 (m,4H), 23 δ = 9.29 (s, 1H), 9.02 (s, 1H), 8.74-8.68 (m, 2H), 8.52-8.48 (m,2H), 522.21 521.21 8.39 (s, 1H), 8.07-8.05 (d, 1H), 7.90-7.88 (d, 1H),7.56-7.47 (m, 6H), 7.08-7.04 (m, 4H), 6.85-6.81 (m, 2H), 6.66-6.63 (m,2H), 6.16-6.13 (m, 4H) 27 δ = 9.29 (s, 1H), 9.02 (s, 1H), 8.73-8.68 (m,2H), 8.52-8.48 (m, 2H), 674.28 673.28 8.39 (s, 1H), 8.07-8.05 (s, 1H),7.90-7.88 (d, 1H), 7.58-7.35 (m, 20H), 6.85-6.81 (m, 4H), 6.62-6.58 (m,2H) 29 δ = 9.29 (m, 1H), 9.02 (m, 1H), 8.74-6.68 (m, 2H), 8.52-8.48 (m,2H), 702.24 701.24 8.39 (m, 1H), 8.07-8.05 (m, 1H), 7.90-7.78 (m, 3H),7.56-7.50 (m, 10H), 7.42-7.36 (m, 6H), 6.98-6.96 (m, 2H), 6.73-6.69 (m,2H), 37 δ = 9.12 (s, 1H), 9.06 (s, 1H), 8.74-8.67 (m, 2H), 8.52-8.48 (m,2H), 698.28 697.28 8.36 (s, 1H), 8.11-8.09 (d, 1H), 8.04-8.02 (d, 1H),7.77-7.75 (d, 2H), 7.62-7.51 (m, 8H), 7.37-7.28 (m, 4H), 7.08-7.05 (m,6H), 6.66-6.63 (m, 2H), 6.16-6.13 (m, 4H) 38 δ = 9.32 (m, 1H), 9.02 (m,1H), 8.74-8.67 (m, 2H), 8.52-8.48 (m, 3H), 572.23 571.23 8.17 (s, 1H),8.06-8.03 (ss, 1H), 7.96-7.94 (ss, 1H), 7.84-7.75 (m, 2H), 7.56-7.48 (m,5H), 7.31-7.30 (d, 1H), 7.08-7.04 (m, 4H), 6.97-6.95 (m, 1H), 6.66-6.63(m, 2H), 6.18-6.16 (m, 4H)

Example 1

A 15 Ω/cm²ITO glass substrate (having a thickness of 1,200 Å, availablefrom Corning) was cut to a size of 50 mm×50 mm×0.7 mm and then sonicatedin isopropyl alcohol and deionized water each for five minutes, and thencleaned by irradiation of ultraviolet rays for 30 minutes and exposureto ozone. The resulting glass substrate with or as an ITO anode wasmounted into a vacuum deposition device.

2-TNATA was vacuum-deposited on the ITO anode of the glass substrate toform an HIL having a thickness of 600 Å, and Compound 1 of SynthesisExample 1 was vacuum-deposited as a hole transport compound to form aHTL having a thickness of about 300 Å.

Next, 9,10-di(naphthalen-2-yl)anthracene (hereinafter, “ADN”) as a bluefluorescent host and N,N,N′,N′-tetraphenyl-pyrene-1,6-diamine(hereinafter, “TPD”) as a blue fluorescent dopant were co-deposited onthe HTL in a weight ratio of about 98:2 to form an EML having athickness of about 300 Å.

Alq₃ was deposited on the EML to form an ETL having a thickness of about300 Å. Subsequently, LiF as a halogenated alkali metal was deposited onthe ETL to form an EIL having a thickness of about 10 Å, and then Al wasvacuum-deposited on the EIL to form a cathode having a thickness ofabout 3,000 Å, thus resulting in a LiF/Al electrode (cathode), therebymanufacturing an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 2, instead of Compound 1, was used toform the HTL.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 5, instead of Compound 1, was used toform the HTL.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 18, instead of Compound 1, was usedto form the HTL.

Example 5

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 22, instead of Compound 1, was usedto form the HTL.

Example 6

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 23, instead of Compound 1, was usedto form the HTL.

Example 7

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 27, instead of Compound 1, was usedto form the HTL.

Example 8

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 29, instead of Compound 1, was usedto form the HTL.

Example 9

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 37, instead of Compound 1, was usedto form the HTL.

Example 10

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 38, instead of Compound 1, was usedto form the HTL.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that NPB, instead of Compound 1, was used to formthe HTL.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound A13, instead of Compound 1, was usedto form the HTL.

Characteristics of the organic light-emitting devices of Examples 1 to10 and Comparative Examples 1 and 2 are shown in Table 2.

TABLE 2 Driving Current Half-life voltage density Luminance EfficiencyEmission span (hr Example HTL material (V) (mA/cm²) (cd/m²) (cd/A) color@100 mA/cm²) Example 1 Compound 1 5.58 50 3090 6.18 blue 295 hr Example2 Compound 2 5.45 50 3095 6.19 blue 298 hr Example 3 Compound 5 5.60 503072 6.14 blue 302 hr Example 4 Compound 18 5.55 50 3095 6.19 blue 290hr Example 5 Compound 22 5.54 50 3101 6.20 blue 305 hr Example 6Compound 23 5.49 50 3150 6.30 blue 315 hr Example 7 Compound 27 5.33 503172 6.34 blue 319 hr Example 8 Compound 29 5.35 50 3169 6.34 blue 328hr Example 9 Compound 37 5.25 50 3177 6.35 blue 306 hr Example 10Compound 38 5.48 50 3205 6.4 blue 295 hr Comparative NPB 7.01 50 26455.29 blue 258 hr Example 1 Comparative A13 7.33 50 2690 5.38 blue 207 hrExample 2

Referring to Table 2, the organic light-emitting devices of Examples 1to 10 (including a compound of Formula 1 in the HTL) were found to havea reduced driving voltage and improved efficiency and lifetimecharacteristics.

As described above, according to the one or more of the aboveembodiments, an organic light-emitting device with a high efficiency,low voltage, high luminance, and long lifespan may be manufactured usinga compound of Formula 1.

The embodiments may provide a compound as a hole transport material thatmay provide an improved efficiency, low voltage, high luminance, andimproved long lifetime characteristics, and an organic light-emittingdevice including the compound.

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims.

What is claimed is:
 1. A compound represented by Formula 1:

wherein, in Formula 1, R₁ to R₃ are each independently selected from asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, and a group represented by Formula 1-1; and atleast one of R₁ to R₃ is a group represented by Formula 1-1:

wherein, in Formula 1-1, X is selected from a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group; mis an integer of 1 to 3, a plurality of Xs being the same or differentwhen m is 2 or 3; and Ar₁ and Ar₂ are each independently selected from asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,wherein at least one substituent of the substituted C₁-C₆₀ alkyl group,the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynylgroup, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group, thesubstituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ arylene group, the substituted C₆-C₆₀ aryloxy group,the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀ heteroarylgroup, the substituted C₁-C₆₀ heteroarylene group, the substitutedmonovalent non-aromatic condensed polycyclic group, the substitutedmonovalent non-aromatic condensed heteropolycyclic group, thesubstituted divalent non-aromatic condensed polycyclic group, and thesubstituted divalent non-aromatic condensed heteropolycyclic group isselected from: a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, and a C₁-C₆₀ alkoxy group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇), a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group,and a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇), wherein Q₁₁ to Q₁₇ and Q₂₁ to Q₂₇are each independently selected from a hydrogen, a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group.
 2. Thecompound as claimed in claim 1, wherein, in Formula 1-1, X is asubstituted or unsubstituted C₆-C₆₀ arylene group or a substituted orunsubstituted C₁-C₆₀ heteroarylene group.
 3. The compound as claimed inclaim 1, wherein, in Formula 1-1, X is a group represented by one ofFormulae 2a, 2b, and 2c:

wherein, in Formulae 2a, 2b, and 2c, * indicates a binding site to anadjacent atom.
 4. The compound as claimed in claim 1, wherein, inFormula 1, Ar₁ and Ar₂ are each independently a substituted orunsubstituted C₆-C₆₀ aryl group or a substituted or unsubstituted C₁-C₆₀heteroaryl group.
 5. The compound as claimed in claim 1, wherein, inFormula 1, An and Ar₂ are each independently a group represented by oneof Formulae 3a, 3b, and 3c:

wherein, in Formulae 3a, 3b, and 3c, H₁ is O or S; Z₁ is selected from ahydrogen, a deuterium, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C20 aryl group, a substitutedor unsubstituted C1-C20 heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;p is an integer of 1 to 7; and * indicates a binding site to aneighboring atom.
 6. The compound as claimed in claim 5, wherein Z₁ is ahydrogen, a deuterium, or a group represented by Formula 4a:

wherein, in Formula 4a, * indicates a binding site to a neighboringatom.
 7. The compound as claimed in claim 1, wherein the compoundrepresented by Formula 1 is represented by Formula 2:

wherein, in Formula 2, X, m, Ar₁, and Ar₂ are defined the same as X, m,Ar₁, and Ar₂ of Formula
 1. 8. The compound as claimed in claim 1,wherein the compound represented by Formula 1 is represented by Formula3:

wherein, in Formula 3, X, m, Ar₁, and Ar₂ are defined the same as X, m,Ar₁, and Ar₂ of Formula
 1. 9. The compound as claimed in claim 1,wherein the compound represented by Formula 1 is one of the followingCompounds 1 to 44, 46, and 47:


10. An organic light-emitting device, comprising: a first electrode; asecond electrode disposed opposite to the first electrode; and anorganic layer between the first electrode and the second electrode, theorganic layer including an emission layer, wherein the organic layerincludes the compound as claimed in claim
 1. 11. The organiclight-emitting device as claimed in claim 10, wherein: the firstelectrode is an anode, the second electrode is a cathode, and theorganic layer includes: a hole transport region between the firstelectrode and the emission layer, the hole transport region including atleast one of a hole injection layer, a hole transport layer, and anelectron blocking layer, and an electron transport region between theemission layer and the second electrode, the electron transport regionincluding at least one of a hole blocking layer, an electron transportlayer, and an electron injection layer.
 12. The organic light-emittingdevice as claimed in claim 11, wherein the hole transport regionincludes the compound.
 13. The organic light-emitting device as claimedin claim 11, wherein: the hole transport region includes the holetransport layer; and the hole transport layer includes the compound. 14.The organic light-emitting device as claimed in claim 11, wherein thehole transport region further includes a charge-generating material. 15.The organic light-emitting device as claimed in claim 14, wherein thecharge-generating material includes a p-dopant.
 16. The organiclight-emitting device as claimed in claim 15, wherein the p-dopantincludes one of a quinone derivative, a metal oxide, and a cyanogroup-containing compound.
 17. The organic light-emitting device asclaimed in claim 11, wherein the electron transport region includes ametal complex.
 18. The organic light-emitting device as claimed in claim11, wherein the electron transport region includes a Li complex.
 19. Theorganic light-emitting device as claimed in claim 11, wherein theelectron transport region includes ET-D1 or ET-D2:


20. A display device, comprising: a thin film transistor, the thin filmtransistor including a source electrode and a drain electrode; and theorganic light-emitting device as claimed in claim 10, wherein the firstelectrode of the organic light-emitting device is electrically connectedto the source electrode or the drain electrode of the thin filmtransistor.